On the Head of a Pin S4
by Bad Day at Black Rock
Summary: The angels call on Dean for help he doesn't want to give.
1. Chapter 1

Author's note: These fics are based on real episodes from Supernatural. The characters and plots belong to the creator and writers for the show. If you want background on the new character you can read the previous episodes.

On the Head of a Pin

They had driven to the nearest motel after Pamela's funeral. Dean was in a piss poor mood; everything that came out of his mouth was sarcastic and bitter. He was tired of burying good people, he was tired of watching friends put through hell and die. Who the hell cared about saving the world if everyone worth while died in the process?

As they walked into the room he tossed his bag into the darkness. "Home crappy home."

Sam flicked on the lights, they were a little more than surprised to see Uriel and Castiel in the room. Uriel stood facing them, while Castiel stood a few feet behind, staring focused on the wall. His body language was stiff, like a soldier waiting for his commands.

"The three amigos." Uriel raised his head with arrogance when he spoke to them.

Dean stared at him in disgust. "Oh come on." These guys had some nerve showing up right now.

"You are needed."

"Needed? We just got back from needed." He spit out.

"You mind your tone with me."

"No, you mind your damn tone with us."

Sam held his hand in front of him as Dean started to approach the angel. "Look, we just got back from Pamela's funeral."

"Yeah, Pamela, the psychic, you remember her right? Cas," he called. "You remember her right? You burned her eyes out. Remember that? Good times."

He looked at him, trying to cover his confusion with serenity.

"Dean calm down." Kayla touched his arm but he pulled away.

"No, she died saving one of their precious seals." He looked back at them. "So maybe you can stop pushing us around like chess pieces for five freaking minutes!"

Uriel didn't even flinch when he yelled. "We raised you out of hell for our purposes."

"Oh and what were those purposes again? Huh? What exactly do you want me for?"

"You can start with gratitude."

"Dean we know this is difficult to understand." Cas offered.

"And _we_, _don't_ care." Uriel shot him a look and Cas looked at the wall again, closing his mouth. "Now, seven angels have already been murdered, all from our garrison. The last one was tonight."

"Demons?" Dean asked; that would be a unique situation. "How are they doing it?"

"More importantly," Sam added. "What are we supposed to do about it? A demon that ices angels is out of our league."

"We have Alastair." Castiel finally came up beside Uriel.

"Great, he should be able to name your trigger man."

"He won't talk. His will is very strong, we've arrived at an impasse."

Dean shrugged. "Yeah well he's like a black belt in torture, you guys are out of your league."

"That's why we've come to his student." Uriel stated. "You happen to be the most qualified interrogator we've got."

"Dean you're our best hope."

His heart stopped. When he could breath again he shook his head. "No, no way. You can't ask me to do this Cas, not this." He couldn't do it again, he could barely stand to glimpse back on the memories of what had already happened.

Uriel stepped closer to them with a smirk. "Who said anything about asking?"

"No, wait…" Kayla caught Uriel by the wrist as he raised his hand towards Dean and suddenly they were in a warehouse.

When Uriel saw that Kayla had come with them he grit his teeth and looked at Castiel. "Send her back, or I'll…"

"You'll _what?_" Dean stepped up to him. "I will kick your ass so hard you're gonna have toes for teeth. Now I wanna talk to Cas, alone."

Uriel grimaced. "I think I'll go seek revelation. We might have some further orders."

"Well get some donuts while you're out."

He chuckled. "This one just won't quit will he? I'm starting to like him." He disappeared.

Kayla heard the wings and turned to Castiel. "Do we ever get to see the wings? Seriously."

Dean shook his head when he just looked at her. "I'm starting to think junkless has a better sense of humor than you do."

"Uriel is the funniest angel in the garrison, ask anyone." Completely deadpan.

"What's going on Cas? Since when does Uriel put a leash on you?"

"My superiors have begun to question my sympathies. I've become too close to the humans in my charge. Namely you and your family. They feel I've begun to express emotions."

Kayla raised an eyebrow. "This is bad?"

"Emotions are the doorway to doubt. It can impair my judgment."

Dean looked at him a moment and walked past him. Apparently he wasn't answering to Cas anymore. "Well you can tell Uriel or whoever, you don't want me doing this. Trust me."

"Want it? No, but I've been told we need it."

"If you open that door and I walk through it, you will not like what walks out."

Kayla heard the struggle in his voice, he was breaking down just thinking about it. She stayed near Castiel. "You can't expect him to do this, it's not right Cas."

"For what it's worth, I'd give anything not to have him do this."

"That's not good enough! You _know_ he shouldn't do this! How can you follow this order?" She tried desperately to reason with him but knew there was no point in it, angels were black and white. Dean bent his head and she went and touched his hand. "You don't have to do this Dean. Tell them no, tell them to go to hell for even suggesting it!"

He searched her expression for an answer. The angels had saved him from hell, but did he really owe them this? Almost everything in her eyes told him not to do it; she knew as much as he did what it would do to him. But then there was the hidden emotion, the one he had to look behind the mask to see. That glint of living terror, the agony burning in the back of her soul.

"I'll do it."

"Dean!"

He slid his hands on either side of her face and kissed her firmly, then rested his forehead against hers. "He's gonna pay for what he did to you."

"You don't have to do that. Alastair's a piece of shit, it's not worth it. You can't."

"I have to." He felt like it was the only thing he could do to start to redeem himself at this point. "It'll be okay."

They watched him take the covered tray through the steel door. Kayla put her hand over her mouth, trying to contain a sob. "Cas."

"Please don't."

"It'll break him, this will ruin him."

"He's strong."

"A man can only take so much! Why would you do this to him?"

"It's God's…"

"Why would God think this is okay?!" He looked at her and she recognized the confusion in his eyes; it was a question he'd already considered. "Why would God think torture is okay, and especially with the cost involved?"

After a brief silence they both flinched when Alistair laughed. "You shouldn't be here for this."

"No. Don't do it Cas."

"I'm sorry." He touched her cheek with the back of his fingers.

She was suddenly sitting back on one of the beds at the hotel. Sam and Ruby were standing over the table looking over some papers. "Son of a bitch."

Sam looked back, not surprised to see her. "You okay?"

"He's going to do it, he's already started."

"Where are they keeping him?"

"It's a warehouse, I didn't get a chance to look around."

Ruby nodded. "I can find it."


	2. Chapter 2

The feeling was familiar. A horrible, wrenching surrender as he gave up his soul for someone he loved. He knew this was a mistake, but Alastair was going to pay. As he uncovered the tray in front of him, Dean ignored his laughs as he prepared the tools.

"I'm sorry," Alastair choked back another cackle. "This is a very serious, very emotional situation, for you. I shouldn't laugh, but I mean, are they serious? They send you to torture me?"

Dean didn't waver his expression. His cold eyes bore into the demon that had caused them so much agony. "You got one chance. One. Tell me who's killing the angels. I want a name."

"You think I'll see all your scary toys and spill my guts?"

"Oh you'll spill your guts one way or another, I just didn't want to ruin my shoes. Now answer the question."

"Or what, you'll work me over? But then, maybe you don't want to. Maybe you're scared to." He mocked.

"I'm here aren't I?"

"Not entirely, you left part of yourself back in the pit. Let's see if we can get the two of you back together shall we?"

He went back to the table. "You're gonna be disappointed."

"You have not disappointed me so far. Come on, you gotta want at least a little revenge for everything I did to you. All the pokes and prods." He could tell he wasn't making leeway as Dean kept his eyes on the table. "No? How about all the things I did to your daddy?"

Dean raised his head but he didn't look at him. He went back to the tools. What to use first? He needed to make a hell of a first impression.

"He was on my rack for over a century you know. John Winchester made a good name for himself."

"You can't stall forever."

"Made him the same offer I made you, every night."

"Just give me the demon's name."

"But he said _nein_ each and every time." He chuckled as he rhymed. "I'll be damned, I couldn't break him. He was made of something unique, the stuff of heroes." Alastair smiled. "Then came Dean, and I thought I was up against it again. But daddy's little girl broke in thirty."

Maybe he should start by cutting out his tongue. At least it would shut him up. Nah, too easy. He snatched the holy water and poured it into a small tin pail.

Alastair grinned when he saw the change in his eyes. "Now we're getting somewhere. Holy water? Come on, grasshopper, you're gonna have to get creative to impress me."

"You know Alastair," he snapped. "Even in hell, I could still dream. And over and over and over, you know what I dreamt? I dreamt of this moment. And believe me, I got a few ideas." He lifted a syringe and drew the holy water from the tin. "Let's get started." He stabbed the needle into his neck and pushed the holy water in.

It only took seconds for the effects. Alastair yelled out as the burning coursed through every vein in his body, leaving a searing path of pain. Dean wouldn't lie to himself, he liked hearing him in pain, he _loved_ that it was Alastair. Still, the sound sent his mind to a darker place. He waited patiently for him to stop writhing.

"Let me know if you want more, there's plenty left."

Alastair nearly growled at him. "Go directly to hell. Do not pass go, do not collect two hundred dollars."

Dean returned to the table. He exchanged the syringe for the knife.

"There's that little pig poker, I was wondering where it went."

Dean poured the holy water over it.

"Do you really think this will fix you? Give you closure? That's just sad. Sad, sad sad…"

Didn't affect him. He walked back to him and slowly, just slowly slid that damn knife into his stomach.

Alastair groaned and grit his teeth through the pain. "I carved you into a new animal Dean, there's no going back."

"Maybe." He stepped in closer. "But now it's my turn to carve." He twisted the blade and Alastair yelled out. The agonized sound sent chills of pleasure through his body that he loved and despised at the same time. Either way it wouldn't stop him, it would only drive him further to what he was going to do to him. After everything he'd been through, he was going to make time for Alastair. And he had all the time in the world…


	3. Chapter 3

Talk about your awkward situations. Kayla and Sam hadn't exactly patched things up, he was still keeping secrets. Now she was stuck with him _and_ Ruby, who she was certain had everything to do with it. Still, she'd keep her mouth shut, at least until they found Dean. She watched Ruby set fire to the four corners of a map on the table.

As the fire burned she focused on Sam, who was looking at the map but listening to Ruby as she spoke the incantation. His expression was firm, he was memorizing, trying to take the whole thing in so he might be able to do it himself in the future. _That's a plus._ At least he wasn't trying to keep her around for everything.

The flames overtook the map and Sam looked at her in concern, Ruby's eyes had turned black.

"Relax, the fire is our friend. Besides, the only part of the map we need is the where's Dean part. _Out._" She commanded and the flames stopped, leaving mostly charred black paper, save for one untouched spot. "There, your brother's there. It's a good thing angel's aren't concerned with hiding their dirty business, they're not used to being spied on. Who'd be stupid enough to try?" She smiled and glanced to Kayla but her emotionless expression turned hers sour as well. "You're welcome."

"Thanks." Kayla picked up the unscathed section of map. "Let's go."

But Sam didn't go for the door. He looked anxious and cast her a side glance. "Can you give us a minute?"

Kayla looked at him. "Excuse me?"

"Just…"

"Are you kidding me right now?! Sam, you can get laid afterwards this isn't…"

"It isn't about that!"

"Then what the hell is so important that you're putting Dean before it?" She yelled at him. Enough was enough. "What the hell is going on?"

"Just tell her Sam, she'll understand." Ruby's voice sounded almost amused.

His eyes reflected guilt from every angle and he wouldn't even look at her.

"Wow. Must be pretty damn huge." She grabbed her bag and headed for the door. "I'll be in the car." She slammed the door behind her.

"She seems bitter with you today."

"Don't worry about it. Ruby, it's been three weeks. I need it."

"Well you don't seem to happy about it."

"You think I want this?"

"It's okay Sam, you can have it."


	4. Chapter 4

Alastair was bleeding and it was by his hand. He was grinning but his teeth were stained with the blood he had coughed up. _Grin all you want you bastard because I'll still enjoy every minute of this._

"You know, it's your professionalism I respect." Alastair told him.

He grabbed the cup of holy water and splashed it into his face, into his open mouth and watched him gag. "Who's murdering the angels?" He poured more into the cup and splashed him again.

He spit more blood onto the floor but now his voice was calm, normal. "Just not getting deep enough. You lack the resources. Reality is too concrete up here. I had that problem with Kayla."

Dean shot him a look.

"You didn't even have to be there I mean, you practically _were_ there."

"Shut up."

"I took some of the worst things you did to souls down in the pit and played the moment in her head like a Friday night movie. Then I did them to her. Think about it Dean, think about the horrible things you did."

"_Shut up."_ But his voice staggered. He didn't know whether or not to believe him, Kayla hadn't told him that. More disgrace swept through him as he thought of Kayla seeing him like that, seeing him rip people apart then having to experience it. Hell it was like he had done it himself.

"Hard to keep a living person alive through something like that, much less conscious. I managed it though." He grinned. "She's a screamer, but I guess you already knew that."

He grabbed him by the face and forced rock salt down his throat. If this fucker wouldn't shut up he'd make him.

Alastair could hardly scream as he choked on the salt. It forced its way through his body, burning its own path. He started coughing up solid matter. "Got something caught in my throat." He paused. "I think it's my throat."

"Well strap in, 'cause I'm just starting to have fun." He went back to the table.

"It was supposed to be your father you know, he was supposed to bring it on. But in the end, it was you."

"Bring what on?" He asked casually. He dipped the knife in holy water, then poured rock salt over it. Ouch. Dean smirked thinking his screaming again.

"You know, same offer every night, you and your dad. But you're the one who said sign me up. And that first time you picked up my blade, the first time you cut into that weeping bitch…that was the first seal."

The idea slammed into him and he tried not to look as shocked as he was. "You're lying." He stopped in front of his face.

Alastair's expression did not mock. "And it is written that the first seal shall be broken when a righteous man sheds blood in hell. As he breaks, so shall it break."

Dean turned and walked back to the table.

"Had to break the first before we could break the others." He inhaled sharply. "When we win, when we bring on the apocalypse and burn this Earth down, we'll owe it all to you. Dean Winchester. Believe me son, I wouldn't lie about this. It's kind of a…religious sort of thing with me." He glanced behind him as he heard the dripping water. The devil's trap was broken, just as Uriel promised it would be.

"I don't think you are lying." Dean admitted without looking at him. "But even if the demons do win," he looked at the knife in his hand. "You won't be there to see it." He turned and his breath caught in his throat, Alastair was released from the trap.

"You should talk to your plumber about the pipes."

He didn't remember the pain as Alastair's fist slammed against his face the first time, the second and third time he remembered and he struggled to remain conscious. Alastair pulled him up by his throat. "You got a lot to learn boy so I'll see you back in class, bright and early Monday morning."

Castiel jerked him back and stabbed Ruby's knife into his chest. As it sent small rays of light through his shoulder, Dean fell hard to the floor.

"Almost, looks like God is on my side today."

Castiel turned his hand and the blade twisted, closer to the heart. With a groan Alastair pulled it out. He attacked Castiel with an ancient spite and managed to hang him on metal spike on the wall.

"Like roaches, you celestials. Now I really wish I knew how to kill you. But all I can do is send you back to heaven."

He began to chant in Latin and a white light shone from first his mouth, then his nose and eyes as well. He was so confused, he didn't understand how this had happened. How did he get through the devil's trap? Suddenly Alastair gagged and was thrown back, he saw Sam enter the room. Kayla ran in after him. She saw Dean first and ran to his side, sliding to the floor next to him. He was no longer conscious.

"Stupid pet tricks." Alastair spit at him.

"Who's murdering the angels? How are they doing it?"

He chuckled. "You think I'm gonna tell you?"

"Yeah, I do." He twisted his hand and Alastair gagged again, his eyes turned white.

Kayla held her hand against Dean's wrist, making sure his pulse kept up and she whispered across the room. "Cas are you okay?"

He nodded but was watching Sam, a little in awe of how powerful he was.

"How are the demons killing the angels?!" He yelled at him.

"I…don't…know!" His voice was forced now, more demonic. There were no jokes.

"Right." He closed his fist and Alastair screamed out. Castiel stood to get a better look.

"It's not us…we're…not doing it!"

"I don't believe you!"

"Lilith is not behind this!" Sam released the pain just enough to let him talk. "She wouldn't kill seven angels. She'd kill a hundred. A thousand."

Sam released him.

"Go ahead, send me back, if you can."

"I'm stronger than that now."

Kayla and Castiel looked at him as he raised his hand again.

"Now I can kill."

Sam wasn't even breaking a sweat as Alastair cried out first in pain, then in terror as light radiated through his skeleton. There was no departure of black smoke. The lights just went out and the body slid to the floor. No doubt Alastair wasn't a good guest in his host.

Kayla looked at him, almost shocked enough to ask questions but there were more important things. "He needs a hospital, Sam, his heartbeat is slowing."


	5. Chapter 5

It wasn't the first time she'd sat in a hospital room, holding Dean's hand as he drifted between life and death. The doctor's had seen him, done the x-rays, treated the heavy wounds and administered the drugs. They did their jobs and Dean was stable. He was still in piss poor condition, but he was stable. Sam hadn't spoken a word to her, just sat in silence on the other side of the room until they saw Castiel walking by. Sam jerked out of his chair and went after him.

Kayla would have followed but she couldn't make herself let go of him.

"Sam."

"Get in there, miracle, now."

"I can't."

"What do you mean you can't?! You and Uriel put him in there, because you can't keep a simple devil's trap together!"

"I don't know what happened, that trap…it shouldn't have broken I'm sorry."

"This whole thing was pointless, demons aren't even killing your soldiers."

"Perhaps Alastair was lying."

"No, he wasn't." Not after what he put him through. He went back to the doorway. When he glanced back, Castiel was gone.

"He's gonna be okay." Kayla assured him, she rubbed the silver angel pendant on her necklace between her fingers.

"How do you know?"

"I still have a little faith." She looked at him with tears in her eyes. "Though admittedly it's not a lot anymore."

His eyes went back to the floor, he hated even making eye contact with her anymore. Not with everything he was hiding from them. "You want something to eat?" She shook her head. "I'll be back."


	6. Chapter 6

Days later Dean sat staring at the wall, pondering what Alastair had told him. In his heart he knew he was telling the truth, he almost couldn't believe he hadn't seen it before. Dean had broken the first seal. He'd started the apocalypse. He hadn't even told Kayla about it, not yet. The thought of her hiding her disgust made him nauseous, and the more realistic thought that she'd still accept him made it worse. There were no sins too great for her to bear.

Castiel appeared next to him, also seeming to be in his own thoughts. "Are you okay?"

"No thanks to you."

"You need to be more careful."

"You need to learn how to manage a damn devil's trap."

His answer amused him despite the serious nature of the conversation they were about to have. Dean treating him as an equal didn't seem like a bad thing. "That's not what I mean. Uriel is dead."

Oh how disappointing. "Was it the demons?"

"He was working against us."

That went in one ear and out the other for him; the idea wasn't surprising at all and he moved to more important things. "Is it true? Did I break the first seal? Did I start all this?"

"Yes."

He looked to the side, completely devastated. He knew it was true, but it was hard hearing it come out of his mouth.

"When we discovered Lilith's plan, we laid siege to hell. We fought to get to you before you…"

"Jumped started the apocalypse."

"We were too late."

"Why didn't you just leave me there then?"

"It's not blame that falls on you Dean. It's fate. The righteous man who begins it, is the only one who can finish it. You have to stop it."

"Lucifer, the apocalypse? What does that mean?" He grimaced when he didn't answer, he wasn't letting him do his usual act. "Don't go disappearing on me you son of a bitch. What does that mean?"

"I don't know." He wished he did. "Dean they don't tell me much. I know, our fate rests with you."

"Then you guys are screwed. I can't do it Cas, it's too big. Alastair was right, I'm not all here. I'm not strong enough." Cas didn't answer him, he didn't even look at him. He looked confused, maybe even disappointed. "Well I guess I'm not the man either of our dads wanted me to be. Find someone else. It's not me."

Cas did do his disappearing act then. He didn't know what to say to Dean, didn't know how to comfort him about his responsibilities. His talk with Anna had confused him, his confrontation with Uriel confused him even more. For the first time in his existence Castiel wasn't sure of himself. He felt lost.

Dean wished then that he hadn't sent Kayla off, she really did need to sleep in a somewhat comfortable bed but he knew that's not what she was doing. She was awake, somewhere, stressing out over every and anything. He could use her now.


	7. Chapter 7

He watched her from the entrance of the church; she sat in the center of a pew, an open bible laid across her lap but her eyes were fixed on the cross hanging on the wall in front of her. She looked at the savior and though she didn't speak, her mind was running rapidly over questions of faith and salvation. Her fingers lay gently on the word of the Lord and she let out a soft sigh, Castiel moved to sit beside her.

She didn't seem surprised with his appearance; instead she offered a small smile before her eyes went back to the cross. The scripture she quoted was already imprinted in her mind. "He will wipe every tear from their eyes. There will be no more death or mourning or crying or pain, for the old order of things has passed away."

He smiled when she raised the text, as if trying to prove the words on the page. "Revelations twenty one."

"If that's how it ends, shouldn't we let it come? God is supposed to condemn Lucifer, He's supposed to start everything new."

"That was meant for God's judgment day. The apocalypse was not to be started by the demons."

"So you're saying it's not true."

"I'm saying, I don't know if it's true."

Kayla looked at him again, this time taking time to study his expression. He didn't try to hide it from her. "Are you okay?"

How strange, to hear it directed towards him. A question of concern, questioning his own well being. "No one has ever asked me that before."

"Well, are you?"

He folded his hands and bent his head, reviewing the last few days' events. Everything was much more complicated now and he wanted answers to these questions. Anna would not provide the serenity he was looking for. "Uriel is dead, he was the one who was killing the angels." She was waiting for him to continue. "He wanted to raise Lucifer, but he needed help. Any angel who would not join him was destroyed."

"I wish I was more surprised by that."

"I didn't think Uriel to be a traitor to our Father." He had trusted him for so long.

"It must be unnerving now, not knowing which orders came from heaven, and which were just Uriel trying to get what he wanted."

He knew she would understand, he knew he should go to her. His eyes raised to meet hers now, a creation of his Father's that he knew he could trust. "There are things that I disagree with, so much that doesn't make sense. I think we should play a larger part in keeping the seals from being broken. I want to help, and they want to watch. I don't know what to do."

She hesitated a moment. "What options are you dealing with?"

"Continue what I've been doing, following orders, keeping my faith and praying that God will see this through. Or, I disobey my orders, try to aid in preventing the apocalypse. Which could get me cast out of heaven. Disobedience is a sin, regardless of your motives."

"Even if you were doing the right thing?"

"Following orders is the right thing." He looked at his hands. "You're not going to tell me what to do are you?" It would be so much simpler if someone would just tell him the right decision.

Her hand slid over his wrist and he didn't pull away. He knew she was showing her trust, her acceptance of him and it had become more of a comfort than anything. "Trust your instincts Cas, as confusing as they may be. If your heart is telling you that these guys are making it up as they go along, ditch 'em. You'll do more good helping us out down here."

"Is that what my heart is telling me? I have doubt, but not certainty. How do you know you're making the right decision?"

"You don't." She sighed. "That's the hard part. But, if God is all that you make Him out to be, he's not going to scorn you for doing what's right. You're trying to save the world here you know?"

"I don't seem to be very successful as of late."

"You can't do it alone. Dean's sarcasm aside, we're here to help. Whatever you need Cas, okay?"

"I…" he searched for the right words, the right emotion he was sure he actually felt. "I appreciate your support. Thank you."

"Anytime. I know you're not supposed to swear in church but…" her voice lowered to a whisper. "Free will is a bitch."

He nodded in agreement of the concept. "Free will is a bitch."

She laughed when she heard him say it, and the sound was a brief but inviting reprieve to the anxiety in his mind. He returned her embrace rather than fighting it.

"Does it get easier?"

"Thinking for yourself? It does…in fact, after awhile, you'll insist on it."

He nodded thoughtfully. "Be cautious when you speak with Dean. He's lost faith in himself."

"I'll take care of Dean."

"I know." He smiled. "Goodnight Kayla."

He was gone before she could respond.


End file.
